A-LevelChemistryOrganic synthesis9701/43 · May/June 2025 · Q910 Marks

(a) Phenylamine, C6H5NH2, and propylamine, CH3CH2CH2NH2, can be produced by different reduction reactions.

(a)(i)Identify an organic compound that can be converted into C6H5NH2 by a reduction reaction. State the reagents and conditions for this reaction. organic compound reagents conditions[2]
(a)(ii)Identify an organic compound that can be converted into CH3CH2CH2NH2 by a reduction reaction. State the reagent for this reaction. organic compound reagent[2]
(a)(iii)Identify a single test that will distinguish between C6H5NH2 and CH3CH2CH2NH2 by producing a white precipitate with only one of these amines. Draw the structure of the compound that is precipitated. testing reagent amine that gives a precipitate structure of the compound that is precipitated:[2]
(b)Describe the relative basicities of C6H5NH2, CH3CH2CH2NH2 and NH3. Explain your answer. < least basic < most basic[4]

Mark scheme

Marking points from the official mark scheme (May/June 2025). The mark or mark type is shown in brackets.

[2] nitrobenzene / C6H5NO2
[2] Sn and HCI
[2] concentrated HCl and heat / boil / reflux
[2] M1: propylamide / propenamide / C2H5CONH2 OR propanenitrile / C2H5CN
[2] M2: LiAlH4
[2] M1: bromine (aq) AND phenylamine / C6H5NH2
[2] M2: correct structure
[4] M1: phenylamine ammonia propylamine
[4] M2: a base has a lone pair that can accept a proton / H+
[4] M3: the lone pair on the nitrogen atom of phenylamine is delocalised into the benzene ring / π-system
[4] M4: propylamine has an electron donating alkyl group

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